A Holt 10-ton track-type tractor works in New York City, ca. 1924. Holt was one of the machinery brands carried by H.O. Penn in its formative years. Holt merged with Best Tractor in 1925 to form Caterpillar. H.O. Penn obtained the New York City franchise for Caterpillar in 1933.
Always There … for 100 Years and Counting H.O. Penn Celebrates Its First Century in Business Bob Cleveland was a man of relentless determination. His grandfather’s legacy as a highway contractor and his own passion for heavy equipment had always burned within him. Above all, he coveted the renowned Caterpillar machinery. So, when the news broke in 1965 that H.O. Penn Machinery Inc., the respected Caterpillar dealership of southern New York and Connecticut, might be available, Bob was electrified. It was déjà vu for Bob. Back in 1948, alongside his brother Roy, they had attempted to acquire H.O. Penn after Hamilton “Ham” O. Penn’s passing. Now, 17 years later, the desire still smoldered. His love for Caterpillar and H.O. Penn had only deepened as they ascended to superstardom in the heavy equipment industry. Bob’s career had been defined by building roads, working on iconic projects like the Garden State Parkway, and his unwavering trust in Caterpillar equipment. Caterpillar’s reliability was unmatched, in Bob’s opinion. The allure of H.O. Penn lay not just in its association with Caterpillar, but also in its reputation for customer service, something Bob had experienced firsthand. And then there was the location, at the heart of New York City’s vast infrastructure and expansion. However, fate initially had other plans. Caterpillar redirected Bob to Pennsylvania, where he, along with his brother, Roy, founded Cleveland Brothers Equipment Company in 1948. He made it a success, but his heart still yearned for H.O. Penn. Little did Bob know that destiny had another chapter in store for him, one where he would have another shot at acquiring H.O. Penn. His unwavering spirit and deep-rooted determination would once again be put to the test. The seeds of the company Bob Cleveland had long coveted were sown in the vibrant aftermath of World War I. As the nation reveled in post-armistice prosperity, the streets of New York bustled with dreams of striking it rich on Wall Street. 3
A wide gauge swamp special Caterpillar Twenty Tractor pulls a Killefer Mole Drain on the operations of Nassau County Mosquito Exterminating commission at Freeport, Long Island, in 1932. Note the wood block bolted to every other track shoe for greater width.
H.O. Penn Machinery’s Jericho Turnpike facility in Mineola, circa 1936.
bustling transportation hub. However, space constraints led Penn to relocate uptown, then to the Port Morris Terminal on 140th Street. Here, the company flourished, offering a vast array of tools and equipment for construction contractors.
But amidst the financial frenzy, Hamilton “Ham” Penn saw riches of a different kind. He envisioned opportunity in machinery and tools, essential for the city’s construction boom. Although a novice in construction, Penn’s passion for building and business was undeniable. He recognized that New York, with its relentless growth, was the ultimate stage for the construction industry.
During the Roaring Twenties, another enterprise was on the rise, one that would soon intersect with Ham Penn’s company, changing its destiny forever.
Few could have foreseen that this young entrepreneur would play a pivotal role in shaping the city. In 1921, he embarked on a partnership venture, creating the Ginsburg-Penn Company. Two years later, he founded the H.O. Penn Machinery Company at the Hudson Terminal in Lower Manhattan.
In the year 1904, the world bore witness to a remarkable invention by engineer and inventor Benjamin Holt — an agricultural tractor equipped with tracks. People marveled at its movement across fields, comparing it to a giant crawling insect. Little did they know that this innovation would eventually lead to the birth of an iconic brand.
The terminal was once the world’s largest office building and a
Hamilton Penn (on phone) in his office with vice-president Ralph L. Johnson, circa 1945. 5
Congratullations H.O. Penn on your 100th 1 Anniversay! weilerproducts.com
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A rebuilt 86,000-lb. Bucyrus-Erie shovel leaves the East River facility, circa 1945.
An Angelo Tomasso Inc. tractor in 1955 repairs a storm-damaged roadway — Tomasso eventually became part of the Tilcon company in New Britain, Conn.
Seen here is the parts counter in Poughkeepsie, circa 1946.
A Caterpillar dozer, likely a D7, is at work beneath the George Washington Bridge, circa 1950.
Years later, in 1925, Holt merged his company, Holt Manufacturing, with the C.L. Best Tractor Company. This union would give rise to an iconic global brand —the Caterpillar Tractor Company. The name itself was a nod to one of Holt’s trademark products. The partnership between Caterpillar and H.O. Penn, a prominent machinery dealer, would take shape as both companies entered their second decade of operation. But before this bond could solidify, they had to navigate the tumultuous waters of the Great Depression, which was triggered by the infamous Wall Street stock market crash of 1929. While the world grappled with the economic catastrophe, construction projects of monumental proportions continued, including the construction of iconic skyscrapers like the Chrysler Building and the Empire State Building. The New Deal, initiated by President Franklin Delano Roosevelt, injected hope into the economy, driving infrastructure development in New York City and beyond. H.O. Penn, like the city it served, thrived. It diversified its product lines, adding renowned brands like Bucyrus-Erie, La Roi, Le Tourneau, Marion, and most notably, Caterpillar tractors. In 1933, H.O. Penn was awarded the Caterpillar territory for New York City and several counties in the state. This alliance significantly boosted H.O. Penn’s fortunes, aligning them with the burgeoning construction projects of the era.
Roy E. (C) and Robert “Bob” W. Cleveland (R).
World War II brought about a shift in focus, with Caterpillar equipment and H.O. Penn playing pivotal roles in the war effort. Bulldozerequipped Caterpillar tractors were employed in constructing defenses, airfields and deconstructing enemy fortifications. Ham Penn, the company’s founder, was among the “dollar-a-year” men who dedicated their expertise to the war effort.
The company expanded, opening facilities on Long Island and in Poughkeepsie, offering not only machinery but also expert engineering and technical services. Their reach extended to engines paired with alternating current generators, providing power to construction sites and various industries.
College-age Tom Cleveland is hard at work in his dorm room, circa 1965. 11
Caterpillar tractors are being loaded on the docks in New York in 1969.
After the war, H.O. Penn expanded into Connecticut territory, anticipating postwar growth and infrastructure development. The demand for construction equipment soared, fueled by returning veterans and a booming population. The company thrived, supplying machinery for the construction of bridges, tunnels, highways and more. However, Ham Penn did not live to see this prosperous era. His sudden death in 1948 paved the way for Ralph Johnson to lead the company through two transformative decades. The 1950s brought the inception of the federal interstate highway system, keeping H.O. Penn busy as it supplied Caterpillar equipment for these colossal projects. By the 1960s, Caterpillar had evolved as an industry leader, known for innovation, while H.O. Penn had forged a reputation for unwavering customer service. The stage was set for a remarkable opportunity, one that Bob Cleveland, who had once sought ownership of the company, would seize in 1965, forever altering the course of H.O. Penn’s history.
The devastation of the terror attack was met with a round-the-clock response from H.O. Penn company technicians and support staff to keep essential debris-clearing machines and generator systems running.
Between 1948 and 1965, H.O. Penn, a company that had its roots in the early 1920s, had grown into one of the premier Caterpillar dealerships. The journey of this company mirrored the rapid advancements in the construction and machinery industry. In 1965, a significant turning point occurred when Robert W. Cleveland learned that Ralph Johnson, the then-owner, intended to sell the company. Without hesitation, Cleveland made his move, eventually becoming the CEO and establishing H.O. Penn as a family business.
employees. This people-oriented spirit became the driving force behind H.O. Penn’s continued success. Their relentless commitment to quality and value, combined with a dedication to meeting or exceeding customer expectations, set them apart in a competitive industry. One memorable example of this commitment involved a ferry company that H.O. Penn assured they would never miss a voyage during the warranty period of their engines. When an engine failed on a holiday, H.O. Penn went to extraordinary lengths to source and deliver the necessary parts, ensuring the ferry service stayed operational.
Under Cleveland’s leadership, the transition was seamless, with a commitment to maintaining the company’s integrity and valuing its
In the 1960s, Caterpillar machines were used for the World Trade Center’s original excavation. In the 2000s, a new generation of Cat machines cleared and re-dug the pit to make way for the development that replaced the Twin Towers. 15
Another story from 1978 showcased the determination of an H.O. Penn service representative. Upon receiving an urgent request for engine repair on a U.S. Navy submarine, the representative embarked on a 24hour journey, spanning Canada and various modes of transportation. This tireless effort enabled the submarine to be back in action in record time.
the company’s ever-increasing commitment to being there for its customers, no matter the circumstances. The evolving landscape of New York City, a global financial hub, posed unique challenges and opportunities. H.O. Penn’s Power Systems division played a crucial role in addressing the city’s growing energy needs, ensuring essential facilities like hospitals and police stations remained operational during citywide blackouts in 1965 and 1977. The generators proved indispensable during these critical moments, underlining the importance of uninterrupted power in a digital age.
In the construction and machinery industry, time is truly money. Downtime can have severe consequences for businesses and infrastructure projects alike. H.O. Penn’s reputation for going above and beyond for its customers became the cornerstone of its growth. In 1968, they opened a state-of-the-art facility in Newington, Conn., and expanded into Poughkeepsie, N.Y., in the following year. This expansion reflected
Natural disasters further tested H.O. Penn’s resolve. Following the Windsor Locks, Conn., tornado in 1979, its generators helped restore
H.O. Penn’s company headquarters in Poughkeepsie, N.Y.
H.O. Penn’s facility in Bloomingburg, N.Y. 16
power to businesses and homes, while Caterpillar-equipped contractors played pivotal roles in recovery efforts. H.O. Penn’s adaptability extended to the progressive computerization of daily life, as its generators provided backup power for data centers critical to the global economy.
The September 11, 2001, terrorist attacks brought unprecedented challenges, but H.O. Penn’s response was unwavering. It supplied critical equipment and supported first responders and trauma teams, tirelessly. The company’s commitment to Managing by Values, a principle focused on creating lasting solutions that benefit all stakeholders, ensured they remained a trusted partner in times of crisis.
Through the decades, H.O. Penn expanded its product line, serving a diverse customer base that ranged from independent contractors to major developers. The company provided equipment and support tailored to the evolving needs of its customers, from earthmoving machinery to compact excavators. As New York City and its surrounding areas evolved, H.O. Penn was there to supply the equipment required for both urban development and environmental stewardship.
As H.O. Penn looks ahead to the next generation, the company’s legacy of commitment to customers, flexibility, and adaptability will continue to be its guiding principles. With a century of success behind the company, the people of H.O. Penn remain dedicated to serving their customers, no matter what challenges the future may hold.
H.O. Penn’s facility on Holtsville, N.Y.
H.O. Penn’s facility in Bronx, N.Y. 17
H.O. Penn’s journey through a century was not just a story of machinery and construction. It was a tale of values, dedication and the commitment to its customers and stakeholders. In 1996 Tom Cleveland officially launched a management principle he aptly named “Managing by Values.” It was more than just a set of words; it was a guiding philosophy that would shape the company’s destiny for years to come.
Tom Cleveland knew that instilling such a philosophy wasn’t an overnight task. He recognized that it would require continuous effort to ensure that every member of the H.O. Penn family understood and embraced these principles. Managing by Values was not just about doing business; rather, it was about achieving success in a way that left no one behind.
Managing by Values wasn’t a mere proclamation of good intentions but a blueprint for success. It was a commitment to ensuring that every decision and practice at H.O. Penn would benefit everyone involved — customers, employees, owners and significant partners like Caterpillar and lenders. This core principle would become the yardstick by which H.O. Penn measured its actions, reflecting the high level of respect and consideration afforded to all customers.
In Tom’s words, it was all about creating “all-win solutions.” The cornerstone of this philosophy was clear: to be successful, one had to ensure success for all key stakeholders. Customers, employees, Caterpillar, financial backers — every piece of the puzzle had to fit together seamlessly. This was the path to lasting success that Tom Cleveland envisioned for H.O. Penn.
H.O. Penn’s facility in Medford, N.Y.
H.O. Penn’s facility in Newington, Conn. 18
When leadership transitioned to CEO Rob Cleveland in 2008, the legacy of Managing by Values didn’t fade; instead, it was etched deeper into the company’s DNA. Rob understood that these values were not just a set of principles on paper; they defined who H.O. Penn was. Customers knew what to expect — they knew the values that H.O. Penn lived by, and they trusted the word given by the company. When H.O. Penn made a promise, they followed through, regardless of the size or importance of the customer. The commitment to values extended to all customers, whether they were large, multigeneration businesses or small startups. H.O. Penn treated everyone with the same level of respect and dedication. They provided face time, offered personal support and shared their cell phone numbers to ensure that customers received assistance whenever needed. As H.O. Penn celebrates its remarkable achievement of being in business for 100 years in 2023, Hamilton Penn would undoubtedly have taken pride in the growth and prosperity his initial vision had laid the foundation for. His actions reflected an ethical and responsible mindset. Those values endured and evolved under the Cleveland family’s leadership, further enhanced through Managing by Values. For President Jeff Mitchell, the key to future success transcends technology and pricing — it also is the enduring philosophy of being a relationship-based business. To Mitchell, regardless of size of the company, H.O. Penn will always maintain those one-on-one relationships with its customers. As H.O. Penn looks ahead to the next generation, its century-long track record of adaptation and evolution bodes well for continued success. CEO Rob Cleveland encapsulates the sentiment best, expressing pride in the legacy of H.O. Penn, its dedication to employees, the company’s integral role in the community, and the firm intention to continue serving customers as they look forward to passing the torch to the next generation.
CEO Rob Cleveland and his family at ConExpoCon/AGG 2023 in Las Vegas for the special events marking H.O. Penn’s 100th anniversary. Rob Cleveland is H.O. Penn’s dealer principal and CEO.
Congratulations H.O. PENN! 19
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Congratuulations to H.O. PENN P FOR 100 YEARS IN BUS SINESS
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